I was raised in a kind of hippie-environment where I could do what I wanted as long as I got acceptable grades and didn't get into trouble. While perhaps as a result me and my siblings are not the most ambitious of people (at least not conventionally so), I can say that I've had a very happy and even successful life so far. Definitely less stressful than that of many of my friends who were raised to be ambitious (and then weren't able to 'satisfy' this ambition).
Could you tell me more about what you did or what happened to you since that 'for a while' period that you describe? I have no desire to prescribe to my friend what he should do, but I'm kind of expecting a personal crisis of sorts in the near future as he seems to be able to only barely managing the ambitious environment he's in and the anxiety-filled, high-pressure life he's led so far. If/when he doesn't succeed, it might shatter his high expectations. I'd love to hear how others dealt with similar situations.